organic compounds
(2E)-1-[2,3-Dichloro-6-methyl-5-(trifluoromethyl)phenyl]-2-(1-phenylethylidene)hydrazine
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, cSequent Scientific Limited, Baikampady, Karnataka, India, and dDepartment of Chemistry, Mangalore University, Mangalagangothri, Mangalore 574 199, India
*Correspondence e-mail: hkfun@usm.my
The title compound, C16H13Cl2F3N2, exists in an E conformation with respect to the C=N bond [1.2952 (11) Å] and the C—N—N=C torsion angle is 175.65 (8)°. The dihedral angle between the benzene rings is 42.09 (4)°. An intramolecular C—H⋯F hydrogen bond generates an S(6) ring. In the crystal, the molecules are linked into [101] chains by C—H⋯F hydrogen bonds.
Related literature
For background to the properties and applications of et al. (2008); Banerjee et al. (2009); Ghavtadze et al. (2008). For related structures, see: Fun et al. (2011a,b). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).
see: BarbazanExperimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812042419/hb6964sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812042419/hb6964Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812042419/hb6964Isup3.cml
Equimolar amount of [2,3-dichloro-6-methyl-5-(trifluoromethyl)phenyl]hydrazine and acetophenone were dissolved in a minimum amount of ethanol, then followed by the addition of 0.5 ml concentrated sulfuric acid. The solution was refluxed for 8 h then cooled to room temperature and poured into ice cold water. The solid product was collected through filtration and then dried using a drying oven at 80°C. The product was redissolved in ethanol for recrystalliziation to give yellow blocks of (I). Melting point: 368 K.
N-bound H atom was located from the difference Fourier map and were refined with a riding model with Uiso(H) = 1.2 Ueq(N) [N–H = 0.8915 Å]. The remaining H atoms were positioned geometrically and refined with a riding model with Uiso(H) = 1.2 or 1.5 Ueq(C) [C–H = 0.95 or 0.98 Å]. A rotating group model was applied to the methyl groups. In the final 1 2 3) were omitted.
two outliners (1 2 2 andData collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).C16H13Cl2F3N2 | F(000) = 736 |
Mr = 361.18 | Dx = 1.515 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9943 reflections |
a = 11.2600 (16) Å | θ = 2.4–32.6° |
b = 11.4025 (17) Å | µ = 0.44 mm−1 |
c = 14.8398 (16) Å | T = 100 K |
β = 123.773 (7)° | Block, yellow |
V = 1583.8 (4) Å3 | 0.32 × 0.26 × 0.22 mm |
Z = 4 |
Bruker SMART APEXII Duo CCD diffractometer | 5714 independent reflections |
Radiation source: fine-focus sealed tube | 5043 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ϕ and ω scans | θmax = 32.6°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS); Bruker, 2009) | h = −17→17 |
Tmin = 0.872, Tmax = 0.911 | k = −17→16 |
22269 measured reflections | l = −22→22 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0515P)2 + 0.4114P] where P = (Fo2 + 2Fc2)/3 |
5714 reflections | (Δ/σ)max = 0.001 |
210 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C16H13Cl2F3N2 | V = 1583.8 (4) Å3 |
Mr = 361.18 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.2600 (16) Å | µ = 0.44 mm−1 |
b = 11.4025 (17) Å | T = 100 K |
c = 14.8398 (16) Å | 0.32 × 0.26 × 0.22 mm |
β = 123.773 (7)° |
Bruker SMART APEXII Duo CCD diffractometer | 5714 independent reflections |
Absorption correction: multi-scan (SADABS); Bruker, 2009) | 5043 reflections with I > 2σ(I) |
Tmin = 0.872, Tmax = 0.911 | Rint = 0.023 |
22269 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 0 restraints |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.49 e Å−3 |
5714 reflections | Δρmin = −0.27 e Å−3 |
210 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.07133 (2) | 0.57463 (2) | 0.919947 (18) | 0.02243 (6) | |
Cl2 | 0.27412 (3) | 0.51560 (3) | 1.16881 (2) | 0.03137 (7) | |
F1 | 0.76376 (7) | 0.64100 (7) | 1.26985 (6) | 0.04073 (19) | |
F2 | 0.72355 (7) | 0.79611 (5) | 1.17471 (5) | 0.02773 (13) | |
F3 | 0.76971 (7) | 0.63239 (6) | 1.12760 (7) | 0.03906 (18) | |
N1 | 0.24945 (8) | 0.64196 (7) | 0.75151 (6) | 0.01758 (13) | |
N2 | 0.21577 (8) | 0.68019 (7) | 0.82355 (6) | 0.01970 (14) | |
H1 | 0.1231 | 0.6830 | 0.7982 | 0.024* | |
C1 | 0.08557 (10) | 0.60301 (8) | 0.46427 (7) | 0.02097 (16) | |
H1A | −0.0116 | 0.6165 | 0.4387 | 0.025* | |
C2 | 0.11987 (11) | 0.56352 (9) | 0.39242 (8) | 0.02343 (17) | |
H2A | 0.0464 | 0.5506 | 0.3184 | 0.028* | |
C3 | 0.26177 (11) | 0.54303 (8) | 0.42924 (8) | 0.02305 (17) | |
H3A | 0.2855 | 0.5160 | 0.3806 | 0.028* | |
C4 | 0.36909 (10) | 0.56246 (8) | 0.53808 (8) | 0.02125 (16) | |
H4A | 0.4660 | 0.5484 | 0.5634 | 0.026* | |
C5 | 0.33508 (9) | 0.60236 (7) | 0.60973 (7) | 0.01782 (15) | |
H5A | 0.4090 | 0.6157 | 0.6836 | 0.021* | |
C6 | 0.19245 (9) | 0.62302 (7) | 0.57366 (7) | 0.01647 (14) | |
C7 | 0.15569 (9) | 0.66423 (7) | 0.65008 (7) | 0.01714 (14) | |
C8 | 0.30910 (9) | 0.65100 (7) | 0.93301 (7) | 0.01651 (14) | |
C9 | 0.45661 (9) | 0.67664 (7) | 0.98943 (7) | 0.01764 (15) | |
C10 | 0.54176 (9) | 0.65007 (7) | 1.10045 (7) | 0.01872 (15) | |
C11 | 0.48613 (10) | 0.60149 (8) | 1.15569 (7) | 0.02078 (16) | |
H11A | 0.5468 | 0.5845 | 1.2309 | 0.025* | |
C12 | 0.34106 (10) | 0.57840 (8) | 1.09936 (7) | 0.01957 (15) | |
C13 | 0.25253 (9) | 0.60334 (8) | 0.98898 (7) | 0.01731 (14) | |
C14 | 0.01767 (10) | 0.72840 (9) | 0.60945 (8) | 0.02298 (17) | |
H14A | 0.0361 | 0.7958 | 0.6565 | 0.034* | |
H14B | −0.0503 | 0.6753 | 0.6102 | 0.034* | |
H14C | −0.0225 | 0.7558 | 0.5353 | 0.034* | |
C15 | 0.51547 (11) | 0.73642 (9) | 0.93086 (8) | 0.02373 (17) | |
H15A | 0.6001 | 0.7824 | 0.9828 | 0.036* | |
H15B | 0.4426 | 0.7885 | 0.8747 | 0.036* | |
H15C | 0.5418 | 0.6770 | 0.8972 | 0.036* | |
C16 | 0.69874 (10) | 0.67904 (8) | 1.16736 (8) | 0.02398 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.01517 (9) | 0.02920 (11) | 0.02257 (11) | −0.00304 (7) | 0.01028 (8) | −0.00384 (7) |
Cl2 | 0.02648 (12) | 0.04378 (15) | 0.02537 (12) | −0.00394 (10) | 0.01537 (10) | 0.00792 (10) |
F1 | 0.0198 (3) | 0.0430 (4) | 0.0341 (4) | −0.0034 (3) | −0.0007 (3) | 0.0151 (3) |
F2 | 0.0243 (3) | 0.0190 (3) | 0.0311 (3) | −0.0060 (2) | 0.0099 (2) | −0.0040 (2) |
F3 | 0.0199 (3) | 0.0342 (3) | 0.0623 (5) | −0.0027 (2) | 0.0223 (3) | −0.0143 (3) |
N1 | 0.0180 (3) | 0.0189 (3) | 0.0170 (3) | 0.0008 (2) | 0.0105 (3) | −0.0012 (2) |
N2 | 0.0173 (3) | 0.0259 (4) | 0.0161 (3) | 0.0032 (3) | 0.0094 (3) | −0.0008 (3) |
C1 | 0.0184 (4) | 0.0250 (4) | 0.0172 (4) | −0.0010 (3) | 0.0084 (3) | −0.0001 (3) |
C2 | 0.0270 (4) | 0.0244 (4) | 0.0171 (4) | −0.0028 (3) | 0.0111 (3) | −0.0015 (3) |
C3 | 0.0314 (5) | 0.0200 (4) | 0.0232 (4) | 0.0004 (3) | 0.0185 (4) | −0.0007 (3) |
C4 | 0.0228 (4) | 0.0206 (4) | 0.0244 (4) | 0.0031 (3) | 0.0157 (4) | 0.0015 (3) |
C5 | 0.0176 (3) | 0.0176 (3) | 0.0181 (3) | 0.0016 (3) | 0.0099 (3) | 0.0014 (3) |
C6 | 0.0168 (3) | 0.0161 (3) | 0.0162 (3) | 0.0004 (3) | 0.0090 (3) | 0.0011 (3) |
C7 | 0.0163 (3) | 0.0177 (3) | 0.0179 (3) | 0.0009 (3) | 0.0098 (3) | 0.0005 (3) |
C8 | 0.0161 (3) | 0.0164 (3) | 0.0171 (3) | 0.0004 (3) | 0.0092 (3) | −0.0019 (3) |
C9 | 0.0168 (3) | 0.0158 (3) | 0.0209 (4) | −0.0007 (3) | 0.0109 (3) | −0.0021 (3) |
C10 | 0.0144 (3) | 0.0156 (3) | 0.0222 (4) | 0.0002 (3) | 0.0077 (3) | −0.0005 (3) |
C11 | 0.0181 (4) | 0.0196 (4) | 0.0195 (4) | 0.0005 (3) | 0.0072 (3) | 0.0025 (3) |
C12 | 0.0185 (4) | 0.0203 (4) | 0.0199 (4) | −0.0006 (3) | 0.0106 (3) | 0.0016 (3) |
C13 | 0.0144 (3) | 0.0185 (3) | 0.0183 (4) | −0.0005 (3) | 0.0086 (3) | −0.0019 (3) |
C14 | 0.0196 (4) | 0.0267 (4) | 0.0234 (4) | 0.0066 (3) | 0.0125 (3) | 0.0042 (3) |
C15 | 0.0228 (4) | 0.0257 (4) | 0.0258 (4) | −0.0059 (3) | 0.0155 (4) | −0.0041 (3) |
C16 | 0.0165 (4) | 0.0191 (4) | 0.0288 (4) | −0.0009 (3) | 0.0079 (3) | 0.0006 (3) |
Cl1—C13 | 1.7309 (9) | C5—H5A | 0.9500 |
Cl2—C12 | 1.7340 (10) | C6—C7 | 1.4833 (12) |
F1—C16 | 1.3414 (12) | C7—C14 | 1.5075 (12) |
F2—C16 | 1.3558 (11) | C8—C13 | 1.4069 (12) |
F3—C16 | 1.3394 (13) | C8—C9 | 1.4139 (12) |
N1—C7 | 1.2952 (11) | C9—C10 | 1.4032 (13) |
N1—N2 | 1.3884 (10) | C9—C15 | 1.5165 (13) |
N2—C8 | 1.3985 (11) | C10—C11 | 1.3936 (13) |
N2—H1 | 0.8915 | C10—C16 | 1.5060 (13) |
C1—C2 | 1.3951 (13) | C11—C12 | 1.3850 (13) |
C1—C6 | 1.4013 (12) | C11—H11A | 0.9500 |
C1—H1A | 0.9500 | C12—C13 | 1.3936 (12) |
C2—C3 | 1.3912 (15) | C14—H14A | 0.9800 |
C2—H2A | 0.9500 | C14—H14B | 0.9800 |
C3—C4 | 1.3958 (14) | C14—H14C | 0.9800 |
C3—H3A | 0.9500 | C15—H15A | 0.9800 |
C4—C5 | 1.3916 (12) | C15—H15B | 0.9800 |
C4—H4A | 0.9500 | C15—H15C | 0.9800 |
C5—C6 | 1.4020 (12) | ||
C7—N1—N2 | 115.99 (7) | C11—C10—C9 | 122.64 (8) |
N1—N2—C8 | 117.97 (7) | C11—C10—C16 | 116.48 (8) |
N1—N2—H1 | 116.3 | C9—C10—C16 | 120.81 (8) |
C8—N2—H1 | 116.5 | C12—C11—C10 | 119.05 (8) |
C2—C1—C6 | 120.91 (8) | C12—C11—H11A | 120.5 |
C2—C1—H1A | 119.5 | C10—C11—H11A | 120.5 |
C6—C1—H1A | 119.5 | C11—C12—C13 | 120.24 (8) |
C3—C2—C1 | 119.96 (9) | C11—C12—Cl2 | 118.45 (7) |
C3—C2—H2A | 120.0 | C13—C12—Cl2 | 121.31 (7) |
C1—C2—H2A | 120.0 | C12—C13—C8 | 120.66 (8) |
C2—C3—C4 | 119.63 (9) | C12—C13—Cl1 | 119.65 (7) |
C2—C3—H3A | 120.2 | C8—C13—Cl1 | 119.69 (7) |
C4—C3—H3A | 120.2 | C7—C14—H14A | 109.5 |
C5—C4—C3 | 120.47 (9) | C7—C14—H14B | 109.5 |
C5—C4—H4A | 119.8 | H14A—C14—H14B | 109.5 |
C3—C4—H4A | 119.8 | C7—C14—H14C | 109.5 |
C4—C5—C6 | 120.44 (8) | H14A—C14—H14C | 109.5 |
C4—C5—H5A | 119.8 | H14B—C14—H14C | 109.5 |
C6—C5—H5A | 119.8 | C9—C15—H15A | 109.5 |
C1—C6—C5 | 118.60 (8) | C9—C15—H15B | 109.5 |
C1—C6—C7 | 120.82 (8) | H15A—C15—H15B | 109.5 |
C5—C6—C7 | 120.57 (7) | C9—C15—H15C | 109.5 |
N1—C7—C6 | 115.64 (7) | H15A—C15—H15C | 109.5 |
N1—C7—C14 | 123.57 (8) | H15B—C15—H15C | 109.5 |
C6—C7—C14 | 120.78 (7) | F3—C16—F1 | 106.72 (9) |
N2—C8—C13 | 118.89 (8) | F3—C16—F2 | 106.25 (8) |
N2—C8—C9 | 121.03 (8) | F1—C16—F2 | 105.61 (8) |
C13—C8—C9 | 119.91 (8) | F3—C16—C10 | 113.04 (8) |
C10—C9—C8 | 117.49 (8) | F1—C16—C10 | 112.18 (8) |
C10—C9—C15 | 122.61 (8) | F2—C16—C10 | 112.51 (8) |
C8—C9—C15 | 119.82 (8) | ||
C7—N1—N2—C8 | 175.65 (8) | C15—C9—C10—C11 | 176.09 (8) |
C6—C1—C2—C3 | 0.26 (14) | C8—C9—C10—C16 | −177.55 (8) |
C1—C2—C3—C4 | −0.15 (14) | C15—C9—C10—C16 | −0.72 (13) |
C2—C3—C4—C5 | −0.14 (14) | C9—C10—C11—C12 | −0.09 (14) |
C3—C4—C5—C6 | 0.32 (13) | C16—C10—C11—C12 | 176.85 (8) |
C2—C1—C6—C5 | −0.09 (13) | C10—C11—C12—C13 | 0.13 (14) |
C2—C1—C6—C7 | −179.58 (8) | C10—C11—C12—Cl2 | 178.90 (7) |
C4—C5—C6—C1 | −0.21 (13) | C11—C12—C13—C8 | 0.68 (13) |
C4—C5—C6—C7 | 179.29 (8) | Cl2—C12—C13—C8 | −178.05 (7) |
N2—N1—C7—C6 | −179.96 (7) | C11—C12—C13—Cl1 | −179.68 (7) |
N2—N1—C7—C14 | 0.51 (13) | Cl2—C12—C13—Cl1 | 1.59 (11) |
C1—C6—C7—N1 | 157.04 (8) | N2—C8—C13—C12 | −176.86 (8) |
C5—C6—C7—N1 | −22.44 (12) | C9—C8—C13—C12 | −1.53 (13) |
C1—C6—C7—C14 | −23.41 (12) | N2—C8—C13—Cl1 | 3.50 (11) |
C5—C6—C7—C14 | 157.11 (8) | C9—C8—C13—Cl1 | 178.83 (6) |
N1—N2—C8—C13 | −131.65 (8) | C11—C10—C16—F3 | 127.38 (9) |
N1—N2—C8—C9 | 53.07 (11) | C9—C10—C16—F3 | −55.61 (12) |
N2—C8—C9—C10 | 176.75 (8) | C11—C10—C16—F1 | 6.65 (12) |
C13—C8—C9—C10 | 1.52 (12) | C9—C10—C16—F1 | −176.35 (8) |
N2—C8—C9—C15 | −0.17 (12) | C11—C10—C16—F2 | −112.26 (10) |
C13—C8—C9—C15 | −175.40 (8) | C9—C10—C16—F2 | 64.74 (12) |
C8—C9—C10—C11 | −0.74 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···F1i | 0.95 | 2.39 | 3.1652 (14) | 139 |
C15—H15A···F2 | 0.98 | 2.38 | 3.1018 (13) | 130 |
Symmetry code: (i) x−1, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C16H13Cl2F3N2 |
Mr | 361.18 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 11.2600 (16), 11.4025 (17), 14.8398 (16) |
β (°) | 123.773 (7) |
V (Å3) | 1583.8 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.44 |
Crystal size (mm) | 0.32 × 0.26 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART APEXII Duo CCD diffractometer |
Absorption correction | Multi-scan (SADABS); Bruker, 2009) |
Tmin, Tmax | 0.872, 0.911 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22269, 5714, 5043 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.758 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.090, 1.02 |
No. of reflections | 5714 |
No. of parameters | 210 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.49, −0.27 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···F1i | 0.95 | 2.39 | 3.1652 (14) | 139 |
C15—H15A···F2 | 0.98 | 2.38 | 3.1018 (13) | 130 |
Symmetry code: (i) x−1, y, z−1. |
Acknowledgements
HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the position of Research Officer under the Research University Grant (1001/PFIZIK/811160).
References
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Hydrazones are important compounds for drug design, as possible ligands for metal complexes, organocatalysis and also for the syntheses of heterocyclic compounds (e.g. Barbazan et al., 2008; Banerjee et al., 2009; Ghavtadze et al., 2008). As part of our ongoing studies in this area (Fun et al., 2011a,b), we now describe the structure of the title compound, (I).
The title compound, as shown in Fig. 1, exists in trans conformation with respect to the C7═N1 bond [C7═N1 = 1.2952 (11) Å]. An S(6) ring is formed via an intramolecular C15—H15A···F2 hydrogen bond (Table 1). The dihedral angle between the benzene rings (C1–C6 & C8–C13) is 42.09 (4)°.
In the crystal, Fig. 2, the molecules are linked into chains along [101] by C1—H1A···F1 hydrogen bonds (Table 1).